69222-20-4

Basic information

• Product Name: deoxypodophyllotoxin
• Synonyms: deoxypodophyllotoxin
• CAS NO: 69222-20-4
• Molecular Formula: C₂₂H₂₂O₇
• Molecular Weight: 398.41
• Mol File: 69222-20-4.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 564.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.304±0.06 g/cm3(Predicted)
• CAS DataBase Reference: deoxypodophyllotoxin(CAS DataBase Reference)
• NIST Chemistry Reference: deoxypodophyllotoxin(69222-20-4)
• EPA Substance Registry System: deoxypodophyllotoxin(69222-20-4)

Safety Data

• Hazardous Substances Data: 69222-20-4(Hazardous Substances Data)

Usage

General Description

Deoxypodophyllotoxin is a chemical compound found in the plant species Podophyllum. It is a lignan with potential antineoplastic and cytotoxic properties, making it a promising candidate for cancer treatment. Deoxypodophyllotoxin has been shown to inhibit the growth of cancer cells by interfering with the normal function of microtubules, which are essential for cell division. deoxypodophyllotoxin has also been reported to induce apoptosis, or programmed cell death, in cancer cells. Additionally, deoxypodophyllotoxin has exhibited anti-inflammatory and immunomodulatory effects, making it a versatile compound with potential for various therapeutic applications. Its promising pharmacological properties have garnered attention for further research and development in the field of oncology and other diseases.

Upstream product

• 75-11-6 diiodomethane 
• 1173-42-8 6,7-demethylenedeoxypodophyllotoxin 
• 74-95-3 1,1-dibromomethane 
• 477-48-5 podophyllotoxone 
• 29943-42-8 Tetrahydro-4H-pyran-4-one 
• 1072-72-6 Tetrahydrothiopyran-4-one 
• 563-80-4 3-methyl-butan-2-one 
• 119-61-9 benzophenone 
• 1191-95-3 cyclobutanone 
• 17931-55-4 bicyclo[3.3.1]nonan-9-one 
• 108-94-1 cyclohexanone 
• 75-07-0 acetaldehyde 
• 77-76-9 2,2-dimethoxy-propane 
• 123-72-8 butyraldehyde 

Downstream Products

• 24150-39-8 deoxypicropodophyllin 
• 60073-37-2 2'-bromo-dehydrodesoxypodophyllotoxin 
• 139219-12-8 5-(2,6-Dibromo-3,4,5-trimethoxy-phenyl)-8H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 128443-52-7 5-methoxypodophyllotoxin 
• 119188-52-2 5-methoxypodophyllotoxin-4-O-β-D-glucoside 
• 321747-09-5 deoxyanhydro-4-isopodophyllol 
• 321747-15-3 C₂₂H₂₄O₇ 
• 25088-82-8 9-deoxyanhydropodophyllol 
• 106636-74-2 4-bromo-4-deoxypodophyllotoxin 
• 1014671-34-1 (-)-podophyllotoxin 
• 1445712-18-4 C₃₃H₂₅N₃O₆ 
• 1445712-19-5 C₃₃H₂₄IN₃O₆ 
• 1445712-20-8 C₃₄H₂₇N₃O₇ 
• 1445712-21-9 C₃₄H₂₇N₃O₇ 

Relevant articles and documents

Asymmetric Chemoenzymatic Synthesis of (?)-Podophyllotoxin and Related Aryltetralin Lignans

(?)-Podophyllotoxin is one of the most potent microtubule depolymerizing agents and has served as an important lead compound in antineoplastic drug discovery. Reported here is a short chemoenzymatic total synthesis of (?)-podophyllotoxin and related aryltetralin lignans. Vital to this approach is the use of an enzymatic oxidative C?C coupling reaction to construct the tetracyclic core of the natural product in a diastereoselective fashion. This strategy allows gram-scale access to (?)-deoxypodophyllotoxin and is readily adaptable to the preparation of related aryltetralin lignans.

Synthesis and Computational Studies Demonstrate the Utility of an Intramolecular Styryl Diels-Alder Reaction and Di-t-butylhydroxytoluene Assisted [1,3]-Shift to Construct Anticancer dl-Deoxypodophyllotoxin

Deoxypodophyllotoxin is a secondary metabolite lignan possessing potent anticancer activity with potential as a precursor for known anticancer drugs, but its use is limited by scarcity from natural sources. We here report the total synthesis of racemic de

Design and synthesis of novel 4'-demethyl-4-deoxypodophyllotoxin derivatives as potential anticancer agents

A group of podophyllotoxin (PPT) derivatives (7a-j) were synthesized by conjugating aryloxyacetanilide moieties to the 4'-hydroxyl of 4'-demethyl-4-deoxypodophyllotoxin (DDPT), and their anticancer activity was evaluated. It was found that the most potent compound 7d inhibited the proliferation of three cancer cell lines with sub to low micromolar IC50 values. Furthermore, it was demonstrated that 7d induced cell cycle arrest in G2/M phase in MGC-803 cells, and regulated the expression of cell cycle check point proteins, such as cyclin A, cyclin B, CDK1, cdc25c, and p21. Finally, 4 mg/kg of 7d reduced the weights and volumes of HepG2 xenografts in mice. Our findings suggest that 7d might be a potential anticancer agent.